N-bromobutanimide → 2-(2-Amino-1,3-thiazol-5-yl)ethan-1-ol

HRID 2107560노트

반응식

HRID 2107560 반응식
Br[N:2]1[C:6](=O)[CH2:5][CH2:4][C:3]1=[O:8].O1C=CCC1.[NH2:14][C:15](N)=[S:16]>O>[NH2:14][C:15]1[S:16][C:5]([CH2:4][CH2:3][OH:8])=[CH:6][N:2]=1

참가 물질

5

반응물 3

HCID 67184N-bromobutanimideHCID 709342,3-DihydrofuranHCID 2723790Thiourea

생성물 1

HCID 136371842-(2-Amino-1,3-thiazol-5-yl)ethan-1-ol

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

To an ice cold suspension of 118.2 g of N-bromosuccinimide in 750 ml of water under a nitrogen atmosphere is added dropwise 75 ml of 2,3-dihydrofuran. The resulting solution is stirred at 0° C. for one hour. Thiourea, 50.5 g, is added and the solution refluxed under a nitrogen atmosphere overnight. The acidic solution is continuously extracted with ethyl acetate for 24 hours The ethyl acetate extract contains mostly succinimide. The aqueous phase is basified with concentrated ammonium hydroxide to a pH of 10-11 and continuously extracted with ethyl acetate for 72 hours. The ethyl acetate extract is cooled and acidified with ethereal hydrogen chloride. The hydrochloride salt oils out of solution and is crystallized from an ethanol-acetonitrile mixture to give 60.1 g of 2-amino-5-thiazoleethanol as the monohydrochloride salt; mp 125°-127° C. (lit. (a) mp 126°-127° C.) lit. (a) Farmaco. Ed. Sci., Vol. 41, pages 483-498 (1986).

후처리

  1. temperaturethe solution refluxed under a nitrogen atmosphere overnight
  2. extractionThe acidic solution is continuously extracted with ethyl acetate for 24 hours The ethyl acetate
  3. extractionextract
  4. extractioncontinuously extracted with ethyl acetate for 72 hours
  5. extractionThe ethyl acetate extract
  6. temperatureis cooled
  7. customThe hydrochloride salt oils out of solution and is crystallized from an ethanol-acetonitrile mixture

출처 및 근거

ORD 기록
ord-b339928a557d43668c409bf95d978da6
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04935424

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